JP5713686B2 - Organic compound, organic light emitting device and image display device - Google Patents
Organic compound, organic light emitting device and image display device Download PDFInfo
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- JP5713686B2 JP5713686B2 JP2011002263A JP2011002263A JP5713686B2 JP 5713686 B2 JP5713686 B2 JP 5713686B2 JP 2011002263 A JP2011002263 A JP 2011002263A JP 2011002263 A JP2011002263 A JP 2011002263A JP 5713686 B2 JP5713686 B2 JP 5713686B2
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- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
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- 238000012545 processing Methods 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 125000006617 triphenylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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Description
本発明は、有機化合物、並びにこれを用いた有機発光素子及び画像表示装置に関する。 The present invention relates to an organic compound, and an organic light emitting device and an image display device using the organic compound.
有機発光素子（有機エレクトロルミネッセンス素子、有機ＥＬ素子）は、一対の電極とこれら電極間に配置される有機化合物層とを有する電子素子である。これら一対の電極から電子及び正孔を注入することにより、有機化合物層中の発光性有機化合物の励起子を生成し、該励起子が基底状態に戻る際に、有機発光素子は光を放出する。 An organic light emitting element (an organic electroluminescence element or an organic EL element) is an electronic element having a pair of electrodes and an organic compound layer disposed between these electrodes. By injecting electrons and holes from the pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and the organic light-emitting element emits light when the excitons return to the ground state. .
有機発光素子の最近の進歩は著しく、その特徴として、低駆動電圧、多様な発光波長、高速応答性、発光デバイスの薄型化・軽量化が可能であることが挙げられる。 Recent advances in organic light-emitting devices are remarkable, and their characteristics include low drive voltage, various emission wavelengths, high-speed response, and the ability to make light-emitting devices thinner and lighter.
ところで、現在までに発光性の有機化合物の創出が盛んに行われている。高性能の有機発光素子を提供するにあたり、発光特性の優れた化合物の創出が重要であるからである。 By the way, creation of a light-emitting organic compound has been actively performed so far. This is because, in providing a high-performance organic light-emitting device, it is important to create a compound having excellent light-emitting characteristics.
これまでに創出された化合物として、例えば、特許文献１にて提案されている下記化合物１−Ａがある。この化合物は下記に示すｆｌｕｏｒａｎｔｈｅｎｏ［８，９−ｋ］ｆｌｕｏｒａｎｔｈｅｎｅを基本骨格として有している。尚、この骨格自体の発光は青発光である。 As a compound created so far, for example, there is the following compound 1-A proposed in Patent Document 1. This compound has the following fluorantheno [8,9-k] fluoranthene as a basic skeleton. The luminescence of the skeleton itself is blue light emission.
また特許文献２では、下記化合物１−Ｂが提案されている。一方、特許文献３では下記化合物１−Ｃが提案されている。尚、下記化合物１−Ｂは、有機ＴＦＴ用材料として開示されている。 Patent Document 2 proposes the following compound 1-B. On the other hand, Patent Document 3 proposes the following compound 1-C. In addition, the following compound 1-B is disclosed as an organic TFT material.
しかし化合物１−Ｃは、発光強度は強いものの、分子の平面性及び対称性が高いために、分子間相互作用が大きい。従って、昇華性が悪い。 However, although the compound 1-C has high emission intensity, the intermolecular interaction is large due to the high planarity and symmetry of the molecule. Therefore, the sublimation property is poor.
ところで有機発光素子において、材料自身の発光量子収率が同じであっても、発光輝度は波長に依存することが知られている。これは、視感度が発光波長に依存するためである。ここで最も視感度が高い波長は５５５ｎｍである。 By the way, in the organic light emitting device, it is known that the light emission luminance depends on the wavelength even if the light emission quantum yield of the material itself is the same. This is because the visibility depends on the emission wavelength. The wavelength with the highest visibility here is 555 nm.
従って、高効率な有機発光素子を得るためには５５５ｎｍ付近（黄色領域）に最大発光波長を有する材料が必要となるが、その開発はまだ十分ではない。 Therefore, in order to obtain a high-efficiency organic light-emitting device, a material having a maximum emission wavelength in the vicinity of 555 nm (yellow region) is required, but its development is not sufficient.
また特許文献１乃至３にて提案されている基本骨格を有する化合物の内、黄色領域の発光を有し、発光効率が良好でかつ昇華性のよい化合物はない。 Further, among the compounds having the basic skeleton proposed in Patent Documents 1 to 3, there is no compound having light emission in the yellow region, good emission efficiency, and good sublimation.
本発明は、上記課題を解決するためになされるものであり、その目的は、基本骨格自体で黄色領域の発光波長を有し、発光効率が高く、昇華性の良好な有機化合物を提供することである。 The present invention has been made in order to solve the above-described problems, and an object of the present invention is to provide an organic compound having a light emission wavelength in a yellow region with a basic skeleton itself, high luminous efficiency, and good sublimation properties. It is.
本発明の有機化合物は、下記一般式（１）に示される構造であることを特徴とする。 The organic compound of the present invention has a structure represented by the following general formula (1).
本発明によれば、基本骨格自体で黄色領域の発光波長を有し、発光効率が高く、昇華性の良好な有機化合物を提供することができる。 According to the present invention, it is possible to provide an organic compound having a light emission wavelength in a yellow region with a basic skeleton itself, high luminous efficiency, and good sublimation properties.
まず本発明に係る有機化合物について説明する。本発明に係る有機化合物は、下記一般式（１）に示される構造である有機化合物である。 First, the organic compound according to the present invention will be described. The organic compound according to the present invention is an organic compound having a structure represented by the following general formula (1).
式（１）において、Ｒ1乃至Ｒ20は、それぞれ水素原子、ハロゲン原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアルコキシ基、置換あるいは無置換のアミノ基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基及び置換あるいは無置換のアリールオキシ基から選ばれる置換基である。本発明において、好ましくは、式（１）中の、Ｒ1乃至Ｒ20は、それぞれ水素原子及び置換あるいは無置換のアリール基から選ばれる置換基である態様である。本発明において、特に好ましくは、Ｒ2及びＲ9が、置換あるいは無置換のアリール基であり、Ｒ1、Ｒ3乃至Ｒ8及びＲ10乃至Ｒ20が水素原子である態様である。 In the formula (1), R 1 to R 20 are each a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl. And a substituent selected from a group, a substituted or unsubstituted heterocyclic group and a substituted or unsubstituted aryloxy group. In the present invention, preferably, R 1 to R 20 in the formula (1) are each a substituent selected from a hydrogen atom and a substituted or unsubstituted aryl group. In the present invention, particularly preferred is an embodiment in which R 2 and R 9 are substituted or unsubstituted aryl groups, and R 1 , R 3 to R 8 and R 10 to R 20 are hydrogen atoms.
Ｒ1乃至Ｒ20で表されるハロゲン原子として、フッ素、塩素、臭素、ヨウ素等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the halogen atom represented by R 1 to R 20 include, but are not limited to, fluorine, chlorine, bromine, iodine and the like.
Ｒ1乃至Ｒ20で表されるアルキル基として、メチル基、エチル基、ノルマルプロピル基、イソプロピル基、ノルマルブチル基、ターシャリーブチル基、セカンダリブチル基、オクチル基、１−アダマンチル基、２−アダマンチル基等が挙げられるが、もちろんこれらに限定されるものではない。この中でも、排除体積の大きいターシャリーブチル基が、昇華性の観点から好ましく、分子構造中に２つ以上のターシャリーブチル基を有するのがより好ましい。ただし、これはＲ1乃至Ｒ20のうちの２つ以上がターシャリーブチル基であることのみを意味するのではない。Ｒ1乃至Ｒ20で表される置換基に導入されるターシャリーブチル基を含めて２つ以上有するのが好ましい、という意味である。 Examples of the alkyl group represented by R 1 to R 20 include methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, secondary butyl group, octyl group, 1-adamantyl group, and 2-adamantyl group. Examples include, but are not limited to, groups. Among these, a tertiary butyl group having a large excluded volume is preferable from the viewpoint of sublimation, and it is more preferable to have two or more tertiary butyl groups in the molecular structure. However, this does not mean that two or more of R 1 to R 20 are tertiary butyl groups. It means that it is preferable to have two or more including a tertiary butyl group introduced into the substituent represented by R 1 to R 20 .
Ｒ1乃至Ｒ20で表されるアルコキシ基として、メトキシ基、エトキシ基、プロポキシ基、２−エチル−オクチルオキシ基、ベンジルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the alkoxy group represented by R 1 to R 20 include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.
Ｒ1乃至Ｒ20で表されるアミノ基として、Ｎ−メチルアミノ基、Ｎ−エチルアミノ基、Ｎ，Ｎ−ジメチルアミノ基、Ｎ，Ｎ−ジエチルアミノ基、Ｎ−メチル−Ｎ−エチルアミノ基、Ｎ−ベンジルアミノ基、Ｎ−メチル−Ｎ−ベンジルアミノ基、Ｎ，Ｎ−ジベンジルアミノ基、アニリノ基、Ｎ，Ｎ−ジフェニルアミノ基、Ｎ，Ｎ−ジナフチルアミノ基、Ｎ，Ｎ−ジフルオレニルアミノ基、Ｎ−フェニル−Ｎ−トリルアミノ基、Ｎ，Ｎ−ジトリルアミノ基、Ｎ−メチル−Ｎ−フェニルアミノ基、Ｎ，Ｎ−ジアニソリルアミノ基、Ｎ−メシチル−Ｎ−フェニルアミノ基、Ｎ，Ｎ−ジメシチルアミノ基、Ｎ−フェニル−Ｎ−（４−ターシャリブチルフェニル）アミノ基、Ｎ−フェニル−Ｎ−（４−トリフルオロメチルフェニル）アミノ基等が挙げられるが、もちろんこれらに限定されるものではない。 As an amino group represented by R 1 to R 20 , an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, an N, N-diethylamino group, an N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N, N-dibenzylamino group, anilino group, N, N-diphenylamino group, N, N-dinaphthylamino group, N, N-diflu Olenylamino group, N-phenyl-N-tolylamino group, N, N-ditolylamino group, N-methyl-N-phenylamino group, N, N-dianisolylamino group, N-mesityl-N-phenylamino group N, N-dimesitylamino group, N-phenyl-N- (4-tertiarybutylphenyl) amino group, N-phenyl-N- (4-trifluoromethylphenyl) amino group and the like. But not of course not limited thereto.
Ｒ1乃至Ｒ20で表されるアリール基として、フェニル基、ナフチル基、インデニル基、ビフェニル基、ターフェニル基、フルオレニル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the aryl group represented by R 1 to R 20 include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, and a fluorenyl group.
Ｒ1乃至Ｒ20で表される複素環基として、ピリジル基、ピリミジル基、ピラジル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、カルバゾリル基、アクリジニル基、フェナントロリル基、ジベンゾチオフェニル基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the heterocyclic group represented by R 1 to R 20 include pyridyl group, pyrimidyl group, pyrazyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, carbazolyl group, acridinyl group, phenanthroyl group, dibenzothiophenyl group and the like. Of course, it is not limited to these.
Ｒ1乃至Ｒ20で表されるアリールオキシ基として、フェノキシ基、４−ターシャルブチルフェノキシ基、チエニルオキシ基等が挙げられるが、もちろんこれらに限定されるものではない。 Examples of the aryloxy group represented by R 1 to R 20 include, but are not limited to, a phenoxy group, a 4-tertiarybutylphenoxy group, and a thienyloxy group.
上記アルキル基、アルコキシ基、アミノ基、アリール基、複素環基及びアリールオキシ基が有する置換基として、メチル基、エチル基、イソプロピル基、ターシャリーブチル基等のアルキル基、ベンジル基等のアラルキル基、フェニル基、ビフェニル基等のアリール基、ピリジル基、ピロリル基等の複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基等のアミノ基、メトキシ基、エトキシ基、プロポキシ等のアルコキシ基、フェノキシ基等のアリールオキシ基、フッ素、塩素、臭素、ヨウ素等のハロゲン原子、シアノ基等が挙げられるが、もちろんこれらに限定されるものではない。 As the substituent of the alkyl group, alkoxy group, amino group, aryl group, heterocyclic group and aryloxy group, an alkyl group such as a methyl group, an ethyl group, an isopropyl group or a tertiary butyl group, or an aralkyl group such as a benzyl group Aryl group such as phenyl group and biphenyl group, heterocyclic group such as pyridyl group and pyrrolyl group, amino group such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group and ditolylamino group, methoxy group, ethoxy group An alkoxy group such as propoxy, an aryloxy group such as phenoxy group, a halogen atom such as fluorine, chlorine, bromine and iodine, a cyano group and the like are, of course, not limited thereto.
次に、本発明に係る有機化合物の合成方法について説明する。本発明に係る有機化合物は、例えば、下記に示される合成スキームに従って合成される。 Next, the method for synthesizing the organic compound according to the present invention will be described. The organic compound according to the present invention is synthesized, for example, according to the synthesis scheme shown below.
このように、本発明に係る有機化合物は、Ｄ１（あるいはその誘導体）又はＤ５（あるいはその誘導体）を出発物質として合成される。 Thus, the organic compound according to the present invention is synthesized using D1 (or a derivative thereof) or D5 (or a derivative thereof) as a starting material.
ここで合成ルート１を利用する場合、化合物Ｄ１、Ｄ２、Ｄ４に適宜置換基を導入することにより、式（１）中のＲ1乃至Ｒ20のいずれかが水素原子から所定の置換基に置換されることになる。ここで導入する置換基としては、アルキル基、ハロゲン原子、フェニル基等が挙げられる。また合成ルート２を利用する場合、化合物Ｄ２、Ｄ５、Ｄ６に適宜置換基を導入することにより、式（１）中のＲ1乃至Ｒ20のいずれかが水素原子から所定の置換基に置換されることになる。 Here, when the synthetic route 1 is used, any one of R 1 to R 20 in the formula (1) is substituted from a hydrogen atom to a predetermined substituent by appropriately introducing a substituent into the compounds D1, D2, and D4. Will be. Examples of the substituent introduced here include an alkyl group, a halogen atom, and a phenyl group. In addition, when the synthetic route 2 is used, any of R 1 to R 20 in the formula (1) is substituted from a hydrogen atom to a predetermined substituent by appropriately introducing a substituent into the compounds D2, D5, and D6. Will be.
また上記合成スキームにおいて、Ｄ１乃至Ｄ６をそれぞれ変えることで種々の有機化合物を合成することができる。その具体例を原料であるＤ１乃至Ｄ６と共に下記表１に示す。 In the above synthesis scheme, various organic compounds can be synthesized by changing each of D1 to D6. Specific examples thereof are shown in Table 1 below together with D1 to D6 as raw materials.
次に、本発明に係る有機化合物の特徴を説明する。 Next, the characteristics of the organic compound according to the present invention will be described.
本発明者は、式（１）に示される有機化合物を発明するに当たり、基本骨格それ自体に注目した。具体的には、基本骨格のみの分子が有する発光波長が所望の発光波長領域に収まるものを提供することを試みた。 Inventing the organic compound represented by the formula (1), the inventor paid attention to the basic skeleton itself. Specifically, an attempt was made to provide a compound having a light emission wavelength of molecules having only a basic skeleton within a desired light emission wavelength region.
ところで所望の発光波長を得るために、基本骨格に特定の置換基を設けて化合物自体の発光波長を調節する方法が知られている。ただしこの方法では、化合物自体の安定性が損なわれる場合がある。 By the way, in order to obtain a desired emission wavelength, a method of adjusting the emission wavelength of the compound itself by providing a specific substituent in the basic skeleton is known. However, this method may impair the stability of the compound itself.
本発明において所望の発光波長領域とは黄色領域のことであり、具体的には５３０ｎｍ以上５８０ｎｍ以下である。 In the present invention, the desired emission wavelength region is a yellow region, specifically, 530 nm or more and 580 nm or less.
本発明に係る有機化合物の基本骨格に相当する化合物は、５３０ｎｍ〜５８０ｎｍの波長領域に最大発光波長をもつ化合物である。このため黄色発光材料となる有機化合物の基本骨格として特に好ましい。 The compound corresponding to the basic skeleton of the organic compound according to the present invention is a compound having a maximum emission wavelength in a wavelength region of 530 nm to 580 nm. For this reason, it is particularly preferable as a basic skeleton of an organic compound that becomes a yellow light emitting material.
次に、本発明の有機化合物に類似する構造を有する比較化合物と比較しながら、本発明に係る有機化合物の特徴を説明する。具体的には、下記式（２）、（３）、（４）にそれぞれ示される化合物と比較しながら説明する。 Next, the characteristics of the organic compound according to the present invention will be described in comparison with a comparative compound having a structure similar to the organic compound of the present invention. Specifically, it demonstrates, comparing with the compound respectively shown by following formula (2), (3), (4).
ここで本発明に係る有機化合物は、下記式（５）に示される基本骨格を有する化合物である。 Here, the organic compound according to the present invention is a compound having a basic skeleton represented by the following formula (5).
ここで発明者らは、式（５）で示される有機化合物にフェニル基が置換された有機化合物と、式（２）、（３）、（４）の有機化合物にフェニル基が置換された化合物との物性（発光特性、昇華性）の比較を行った。結果を下記表２に示す。尚、下記表２に示される評価のうち発光波長についてはＦ４５００で測定を行って評価した。また発光量子収率については、絶対量子収率系（浜松ホトニクス製）で測定を行った。さらに昇華性は、真空度約５．０×１０-4Ｐａの条件下でサンプルを加熱した際の評価を示している。 Here, the inventors have an organic compound in which a phenyl group is substituted for the organic compound represented by the formula (5), and a compound in which the organic compound of the formulas (2), (3), and (4) is substituted with a phenyl group. And physical properties (emission characteristics, sublimation properties) were compared. The results are shown in Table 2 below. In addition, about the light emission wavelength among the evaluation shown by following Table 2, it measured by F4500 and evaluated. The light emission quantum yield was measured using an absolute quantum yield system (manufactured by Hamamatsu Photonics). Further, the sublimation property indicates an evaluation when the sample is heated under a condition of a vacuum degree of about 5.0 × 10 −4 Pa.
表２において、化合物（１）は、本発明に係る有機化合物の基本骨格に含まれるペリレン環部分をナフタレン環にした化合物である。表２より、化合物（１）は発光波長（４５８ｎｍ）から青色発光を示す化合物である。しかしこの発光は、本発明で要求される発光特性（黄色発光）とは大きく異なる。 In Table 2, compound (1) is a compound in which the perylene ring portion contained in the basic skeleton of the organic compound according to the present invention is a naphthalene ring. From Table 2, the compound (1) is a compound that emits blue light from the emission wavelength (458 nm). However, this light emission is significantly different from the light emission characteristics (yellow light emission) required in the present invention.
表２において、化合物（２）は、本発明に係る有機化合物の基本骨格に含まれる複数あるナフタレン環部分の一つがピレン環に置き換わった化合物である。表２より、化合物（２）は、本発明に係る有機化合物とは全く異なる骨格を持っているが、ほぼ同様な発光領域で発光する。また、発光量子収率も、本発明に係る有機化合物に比べ若干小さいくらいでほぼ同じ値である。しかし昇華性に関しては本発明に係る有機化合物とは明らかに異なる。即ち、本発明に係る有機化合物に比べて昇華性が明らかに低い。これは、上記ナフタレン環部分がピレン環に置き換わることで分子量が増大したからである。また分子のπ電子面が大きくなったことにより、分子間相互作用が本発明に係る有機化合物よりも強くなったからでもある。 In Table 2, compound (2) is a compound in which one of a plurality of naphthalene ring moieties contained in the basic skeleton of the organic compound according to the present invention is replaced with a pyrene ring. From Table 2, compound (2) has a completely different skeleton from the organic compound according to the present invention, but emits light in substantially the same light emitting region. Further, the light emission quantum yield is almost the same value as it is slightly smaller than the organic compound according to the present invention. However, the sublimation property is clearly different from the organic compound according to the present invention. That is, the sublimation property is clearly lower than that of the organic compound according to the present invention. This is because the molecular weight was increased by replacing the naphthalene ring portion with a pyrene ring. This is also because the intermolecular interaction is stronger than that of the organic compound according to the present invention due to an increase in the π-electron surface of the molecule.
表２において、化合物（３）は、２つのナフタレン環と１つのペリレン環とを含む基本骨格を有する点から考えると、本発明に係る有機化合物の異性体といえる。表２より、化合物（３）は発光波長（５９７ｎｍ）から赤色発光を示す化合物である。しかしこの発光は、本発明で要求される発光特性（黄色発光）とは大きく異なる。また、化合物（３）は、昇華時に分解を伴うことが判明している。ここで昇華時において化合物の分解が伴うと、発光素子の駆動寿命の低下を引き起こす原因となる。このため化合物（３）は、発光素子用材料としては好ましくないといえる。 In Table 2, compound (3) can be said to be an isomer of the organic compound according to the present invention in view of having a basic skeleton containing two naphthalene rings and one perylene ring. From Table 2, the compound (3) is a compound that emits red light from the emission wavelength (597 nm). However, this light emission is significantly different from the light emission characteristics (yellow light emission) required in the present invention. Further, it has been found that the compound (3) is decomposed during sublimation. Here, when the compound is decomposed during sublimation, it may cause a decrease in the driving life of the light emitting element. Therefore, it can be said that the compound (3) is not preferable as a material for a light emitting device.
以上より、所望の発光波長を持ちつつ高い量子収率と高い昇華性とを併せ持つ骨格は、本発明にかかる有機化合物のみである。 As described above, the skeleton having both a high quantum yield and a high sublimation property while having a desired emission wavelength is only the organic compound according to the present invention.
また、本発明に係る有機化合物の基本骨格となる化合物は平面性が高い分子である。このため、薄膜状にすると分子間で重なる（スタッキングが生じる）可能性が高い。そうなると、分子本来の発光（モノマー発光）と共に分子本来の発光に対して著しく長波長化した発光（エキシマー発光）も生じるため好ましくない。これを回避するために、式（１）にて示される基本骨格に置換基を導入するのが好ましい。特に、式（１）中のＲ1、Ｒ2、Ｒ9及びＲ10のいずれかにアリール基を導入すると、導入したアリール基の面が基本骨格平面に対してより垂直に近い形に位置するので、スタッキングの防止に効果的である。 Moreover, the compound which becomes the basic skeleton of the organic compound according to the present invention is a molecule having high planarity. For this reason, when it is made into a thin film, there is a high possibility of overlapping between molecules (stacking occurs). In this case, light emission (excimer light emission) that is significantly longer than the original light emission of the molecule is generated together with the original light emission of the molecule (monomer light emission). In order to avoid this, it is preferable to introduce a substituent into the basic skeleton represented by the formula (1). In particular, when an aryl group is introduced into any of R 1 , R 2 , R 9, and R 10 in formula (1), the plane of the introduced aryl group is positioned closer to the basic skeleton plane. Therefore, it is effective for preventing stacking.
ところで本発明に係る有機化合物は、骨格内に２つの５員環構造を有するため、化合物のＨＯＭＯエネルギーレベルが低い。これは化合物の酸化電位が低いことを意味する。従って、本発明に係る有機化合物は酸化に対して安定である。 By the way, since the organic compound according to the present invention has two five-membered ring structures in the skeleton, the HOMO energy level of the compound is low. This means that the oxidation potential of the compound is low. Therefore, the organic compound according to the present invention is stable against oxidation.
また本発明に係る有機化合物は、基本骨格に窒素原子等のヘテロ原子を有していない。このことも化合物自体の酸化電位が低いことに寄与するものであり、本発明に係る有機化合物が酸化に対して安定であることを示す理由の一つである。 The organic compound according to the present invention does not have a hetero atom such as a nitrogen atom in the basic skeleton. This also contributes to the low oxidation potential of the compound itself, and is one of the reasons that the organic compound according to the present invention is stable against oxidation.
本発明に係る有機化合物の基本骨格は、ＨＯＭＯエネルギーレベルが低い骨格である。即ち、本発明に係る有機化合物の基本骨格は、ＬＵＭＯエネルギーレベルも低い骨格である。 The basic skeleton of the organic compound according to the present invention is a skeleton having a low HOMO energy level. That is, the basic skeleton of the organic compound according to the present invention is a skeleton having a low LUMO energy level.
ところで本発明に係る有機化合物に含まれる基本骨格に、発光波長を長波長化する置換基を導入することで本発明に係る有機化合物を赤色の発光材料とすることもできる。置換基の導入により発光波長が長波長化した材料についても基本骨格自体が本発明に係る有機化合物と同一であるので、酸化に対して安定である。ここで発光波長を長波長化する置換基としては、トリアリールアミンに由来する置換基やアントラセンに由来する置換基等が挙げられる。 By the way, the organic compound according to the present invention can be made into a red light emitting material by introducing a substituent for increasing the emission wavelength into the basic skeleton contained in the organic compound according to the present invention. A material whose emission wavelength is increased by the introduction of a substituent is also stable against oxidation since the basic skeleton itself is the same as the organic compound according to the present invention. Here, examples of the substituent for increasing the emission wavelength include a substituent derived from triarylamine and a substituent derived from anthracene.
上記一般式（１）における化合物の具体例を以下に示す。しかし、本発明はこれらに限られるものではない。尚、以下に列挙される具体例のうち、ＸＸ−１、ＸＸ−２、ＸＸ−４乃至ＸＸ−１０、ＸＸ−１３乃至ＸＸ−１６、ＸＹ−１乃至ＸＹ−８、ＺＺ−１及びＺＺ−４は、本発明に該当する。 Specific examples of the compound in the general formula (1) are shown below. However, the present invention is not limited to these. Of the specific examples listed below, XX-1, XX-2, XX-4 to XX-10, XX-13 to XX-16, XY-1 to XY-8, ZZ-1 and ZZ- No. 4 corresponds to the present invention.
上記例示化合物のうちＸＸ群及びＸＹ群に属する化合物は分子全体が炭化水素のみで構成されている。炭化水素のみで構成される化合物は、一般的にＨＯＭＯエネルギーレベルが低い。従って、ＸＸ群及びＸＹ群に属する化合物は酸化電位が低い、即ち、酸化に対して安定である有機化合物であることを意味する。 Of the above exemplified compounds, the compounds belonging to the XX group and the XY group are composed entirely of hydrocarbons. Compounds composed solely of hydrocarbons generally have a low HOMO energy level. Accordingly, it means that the compounds belonging to the XX group and the XY group are organic compounds having a low oxidation potential, that is, stable to oxidation.
従って、本発明に係る有機化合物のうち、炭化水素のみで構成されている有機化合物、即ち、ＸＸ群、ＸＹ群に属する化合物は、分子の安定性が高いので好ましい。 Therefore, among the organic compounds according to the present invention, organic compounds composed only of hydrocarbons, that is, compounds belonging to the XX group and the XY group are preferable because of high molecular stability.
一方、上記例示化合物のうち、ＺＺ群に属するものは置換基がヘテロ原子を含んでいる。この場合、分子自体の酸化電位が大きく変化する。あるいは分子間相互作用が変化する。また置換基がヘテロ原子を含む場合、最大発光波長を長波長化させることができる。さらに置換基がヘテロ原子を含んでいるＺＺ群の有機化合物は、電子輸送性やホール輸送性、ホールトラップ型発光材料として有用である。またＺＺ群に属する有機化合物は、１００％の高濃度で使用することもできる。 On the other hand, among the above exemplified compounds, those belonging to the ZZ group have a substituent containing a hetero atom. In this case, the oxidation potential of the molecule itself changes greatly. Or intermolecular interaction changes. Moreover, when a substituent contains a hetero atom, the maximum light emission wavelength can be lengthened. Furthermore, an organic compound of ZZ group in which the substituent includes a hetero atom is useful as an electron transport property, a hole transport property, or a hole trap type light emitting material. In addition, organic compounds belonging to the ZZ group can be used at a high concentration of 100%.
以上のように例示化合物をＸＸ群、ＸＹ群及びＺＺ群として挙げた。これら有機化合物は、基本骨格自体で黄色発光するものである。また本発明に係る有機化合物の基本骨格に置換基を適宜設けることにより、発光色が黄色からさらに長波長化した発光、具体的には赤色になり得る。 As described above, the exemplified compounds are listed as the XX group, the XY group, and the ZZ group. These organic compounds emit yellow light with the basic skeleton itself. Further, by appropriately providing a substituent in the basic skeleton of the organic compound according to the present invention, the emission color can be emitted from yellow to a longer wavelength, specifically red.
次に、本発明の有機発光素子について説明する。 Next, the organic light emitting device of the present invention will be described.
本発明の有機発光素子は、一対の電極である陽極と陰極と、これら電極間に配置される有機化合物層と、を少なくとも有する。本発明の有機発光素子において、有機化合物層は発光層を有していれば単層であってもよいし複数層からなる積層体であってもよい。 The organic light emitting device of the present invention has at least a pair of electrodes, an anode and a cathode, and an organic compound layer disposed between these electrodes. In the organic light emitting device of the present invention, the organic compound layer may be a single layer or a laminate composed of a plurality of layers as long as it has a light emitting layer.
ここで有機化合物層が複数層からなる積層体である場合、有機化合物層は、発光層の他に、ホール注入層、ホール輸送層、電子ブロッキング層、ホール・エキシトンブロッキング層、電子輸送層、電子注入層等を有してもよい。また発光層は、単層であってもよいし、複数の層からなる積層体であってもよい。 When the organic compound layer is a laminate composed of a plurality of layers, the organic compound layer includes, in addition to the light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron An injection layer or the like may be included. In addition, the light emitting layer may be a single layer or a laminate including a plurality of layers.
本発明の有機発光素子において、素子を構成する有機化合物層のうち少なくとも一層には本発明に係る有機化合物が含まれている。具体的には、本発明に係る有機化合物は、上述した発光層、ホール注入層、ホール輸送層、電子ブロッキング層、発光層、ホール・エキシトンブロッキング層、電子輸送層、電子注入層等のいずれかに含まれている。本発明の係る有機化合物は、好ましくは、発光層に含まれる。特に、黄色発光素子のゲスト材料として用いられることが好ましい。 In the organic light-emitting device of the present invention, at least one of the organic compound layers constituting the device contains the organic compound according to the present invention. Specifically, the organic compound according to the present invention is any of the above-described light emitting layer, hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole / exciton blocking layer, electron transport layer, electron injection layer, and the like. Included. The organic compound according to the present invention is preferably contained in the light emitting layer. In particular, it is preferably used as a guest material for a yellow light-emitting element.
本発明の有機発光素子において、本発明に係る有機化合物が発光層に含まれる場合、発光層は、本発明に係る有機化合物のみからなる層であってもよいし、本発明に係る有機化合物と他の化合物とからなる層であってもよい。ここで、発光層が本発明に係る有機化合物と他の化合物とからなる層である場合、本発明に係る有機化合物は、発光層のホストとして使用してもよいし、ゲストとして使用してもよい。また発光層に含まれ得るアシスト材料として使用してもよい。 In the organic light emitting device of the present invention, when the organic compound according to the present invention is contained in the light emitting layer, the light emitting layer may be a layer composed only of the organic compound according to the present invention, It may be a layer composed of other compounds. Here, when the light emitting layer is a layer composed of the organic compound according to the present invention and another compound, the organic compound according to the present invention may be used as a host of the light emitting layer or as a guest. Good. Moreover, you may use as an assist material which may be contained in a light emitting layer.
ここでホストとは、発光層を構成する化合物の中で重量比が最も大きい化合物である。またゲストとは、発光層を構成する化合物の中で重量比がホストよりも小さい化合物であって、主たる発光を担う化合物である。またアシスト材料とは、発光層を構成する化合物の中で重量比がホストよりも小さく、ゲストの発光を補助する化合物である。尚、アシスト材料は、第２のホストとも呼ばれている。 Here, the host is a compound having the largest weight ratio among the compounds constituting the light emitting layer. The guest is a compound having a weight ratio smaller than that of the host among the compounds constituting the light-emitting layer and responsible for main light emission. The assist material is a compound that assists the light emission of the guest among the compounds constituting the light emitting layer, having a weight ratio smaller than that of the host. The assist material is also called a second host.
ここで、本発明に係る有機化合物を発光層のゲストとして用いる場合、ゲストの濃度は、発光層全体に対して０．０１重量％以上２０重量％以下であることが好ましく、０．２重量％以上５重量％以下であることがより好ましい。ここで本発明に係る有機化合物を発光層のゲストとして用いて、本発明に係る有機化合物を発光させることで黄色発光する有機発光素子を提供することができる。 Here, when the organic compound according to the present invention is used as a guest of the light emitting layer, the concentration of the guest is preferably 0.01 wt% or more and 20 wt% or less with respect to the entire light emitting layer, and is 0.2 wt%. More preferably, it is 5% by weight or less. Here, by using the organic compound according to the present invention as a guest of the light emitting layer and emitting the organic compound according to the present invention, an organic light emitting element that emits yellow light can be provided.
また本発明に係る有機化合物を発光層のゲストとして用いる際には、本発明に係る有機化合物よりもＬＵＭＯが高い材料（ＬＵＭＯが真空準位により近い材料）をホストとして用いることが好ましい。というのも本発明に係る有機化合物はＬＵＭＯが低いため、本発明に係る有機化合物よりもＬＵＭＯが高い材料をホストにすることで、発光層のホストに供給される電子を本発明に係る有機化合物がより良好に受領することができるからである。 In addition, when the organic compound according to the present invention is used as a guest in the light-emitting layer, a material having a LUMO higher than that of the organic compound according to the present invention (a material whose LUMO is closer to the vacuum level) is preferably used as the host. This is because the organic compound according to the present invention has a low LUMO. Therefore, by using a material having a higher LUMO than the organic compound according to the present invention as a host, the electrons supplied to the host of the light-emitting layer can be used as the organic compound according to the present invention. Because it can be better received.
一方で、本発明に係る有機化合物は赤色発光層のホストとしても用いることができる。 On the other hand, the organic compound according to the present invention can also be used as a host of the red light emitting layer.
本発明者らは種々の検討を行い、本発明に係る有機化合物を、発光層のホスト又はゲストとして、特に、発光層のゲストとして用いると、高効率で高輝度な光出力を有し、かつ極めて耐久性が高い素子が得られることを見出した。この詳細については、後述する実施例で詳しく説明する。 The present inventors have made various studies, and when the organic compound according to the present invention is used as a host or guest of a light emitting layer, in particular, as a guest of a light emitting layer, it has a light output with high efficiency and high brightness, and It has been found that a device with extremely high durability can be obtained. Details of this will be described in detail in an embodiment described later.
一方で、本発明に係る有機化合物は、本発明の有機発光素子を構成する発光層以外の有機化合物層の構成材料として使用することができる。具体的には、電子輸送層、電子注入層、ホール輸送層、ホール注入層、ホールブロッキング層等の構成材料として用いてもよい。この場合、有機発光素子の発光色は赤に限られない。より具体的には白色でもよいし、中間色でもよい。 On the other hand, the organic compound which concerns on this invention can be used as a constituent material of organic compound layers other than the light emitting layer which comprises the organic light emitting element of this invention. Specifically, it may be used as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, or the like. In this case, the emission color of the organic light emitting element is not limited to red. More specifically, it may be white or an intermediate color.
ここで、本発明に係る有機化合物以外にも、必要に応じて従来公知の低分子系及び高分子系のホール注入性化合物あるいはホール輸送性化合物、ホストとなる化合物、発光性化合物、電子注入性化合物あるいは電子輸送性化合物等を一緒に使用することができる。 Here, in addition to the organic compound according to the present invention, conventionally known low-molecular and high-molecular hole-injecting compounds or hole-transporting compounds, compounds serving as hosts, light-emitting compounds, and electron-injecting properties as necessary. A compound or an electron transporting compound can be used together.
以下にこれらの化合物例を挙げる。 Examples of these compounds are given below.
ホール注入性化合物、ホール輸送性化合物としては、ホール移動度が高い材料であることが好ましい。正孔注入性能あるいは正孔輸送性能を有する低分子及び高分子系材料としては、トリアリールアミン誘導体、フェニレンジアミン誘導体、スチルベン誘導体、フタロシアニン誘導体、ポルフィリン誘導体、ポリ（ビニルカルバゾール）、ポリ（チオフェン）、その他導電性高分子が挙げられるが、もちろんこれらに限定されるものではない。 The hole injecting compound and the hole transporting compound are preferably materials having high hole mobility. Low molecular and high molecular weight materials having hole injection performance or hole transport performance include triarylamine derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly (vinylcarbazole), poly (thiophene), In addition, although a conductive polymer is mentioned, of course, it is not limited to these.
ホストとしては、具体的には、下記表３に示される化合物が挙げられる。 Specific examples of the host include compounds shown in Table 3 below.
ただし本発明はこれらに限定されるものではない。表３で示されている化合物の誘導体である化合物もホストとして使用することができる。またそれ以外にも、縮環化合物（例えばフルオレン誘導体、ナフタレン誘導体、アントラセン誘導体、ピレン誘導体、カルバゾール誘導体、キノキサリン誘導体、キノリン誘導体等）、トリス（８−キノリノラート）アルミニウム等の有機アルミニウム錯体、有機亜鉛錯体、及びトリフェニルアミン誘導体、ポリ（フルオレン）誘導体、ポリ（フェニレン）誘導体等の高分子誘導体が挙げられるが、もちろんこれらに限定されるものではない。 However, the present invention is not limited to these. Compounds that are derivatives of the compounds shown in Table 3 can also be used as hosts. In addition, fused ring compounds (for example, fluorene derivatives, naphthalene derivatives, anthracene derivatives, pyrene derivatives, carbazole derivatives, quinoxaline derivatives, quinoline derivatives, etc.), organoaluminum complexes such as tris (8-quinolinolato) aluminum, organozinc complexes And polymer derivatives such as a triphenylamine derivative, a poly (fluorene) derivative, and a poly (phenylene) derivative, but of course not limited thereto.
電子注入性化合物、電子輸送性化合物としては、ホール注入性化合物、ホール輸送性化合物のホール移動度とのバランス等を考慮した上で適宜選択される。電子注入性能あるいは電子輸送性能を有する化合物としては、オキサジアゾール誘導体、オキサゾール誘導体、ピラジン誘導体、トリアゾール誘導体、トリアジン誘導体、キノリン誘導体、キノキサリン誘導体、フェナントロリン誘導体、有機アルミニウム錯体等が挙げられるが、もちろんこれらに限定されるものではない。 The electron injecting compound and the electron transporting compound are appropriately selected in consideration of the balance with the hole mobility of the hole injecting compound and the hole transporting compound. Examples of compounds having electron injection performance or electron transport performance include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, etc. It is not limited to.
陽極の構成材料としては、仕事関数がなるべく大きいものがよい。例えば、金、白金、銀、銅、ニッケル、パラジウム、コバルト、セレン、バナジウム、タングステン等の金属単体あるいはこれら金属単体を複数組み合わせてなる合金、酸化錫、酸化亜鉛、酸化インジウム、酸化錫インジウム（ＩＴＯ）、酸化亜鉛インジウム等の金属酸化物である。また、ポリアニリン、ポリピロール、ポリチオフェン等の導電性ポリマーでもよい。これらの電極物質は１種類を単独で使用してもよいし複数種を併用して使用してもよい。また、陽極は一層構成でもよく、多層構成でもよい。 As a constituent material of the anode, a material having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, or alloys formed by combining a plurality of these metals, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO ), Metal oxides such as indium zinc oxide. Further, conductive polymers such as polyaniline, polypyrrole, and polythiophene may be used. These electrode materials may be used alone or in combination of two or more. Further, the anode may have a single layer structure or a multilayer structure.
一方、陰極の構成材料としては、仕事関数が小さいものがよい。例えば、リチウム等のアルカリ金属、カルシウム等のアルカリ土類金属、アルミニウム、チタニウム、マンガン、銀、鉛、クロム等の金属単体が挙げられる。あるいはこれら金属単体を複数組み合わせた合金も使用することができる。例えば、マグネシウム−銀、アルミニウム−リチウム、アルミニウム−マグネシウム等が使用できる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。これらの電極物質は１種類を単独で使用してもよいし、複数種を併用して使用してもよい。また、陰極は一層構成でもよく、多層構成でもよい。 On the other hand, the material constituting the cathode is preferably a material having a small work function. Examples thereof include alkali metals such as lithium, alkaline earth metals such as calcium, and simple metals such as aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, an alloy obtained by combining a plurality of these metals alone can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, etc. can be used. A metal oxide such as indium tin oxide (ITO) can also be used. One of these electrode materials may be used alone, or a plurality of these electrode materials may be used in combination. Further, the cathode may have a single layer structure or a multilayer structure.
本発明の有機発光素子において、本発明に係る有機化合物を含有する層及びその他の有機化合物からなる層は、以下に示す方法により形成される。一般には真空蒸着法、イオン化蒸着法、スパッタリング、プラズマあるいは、適当な溶媒に溶解させて公知の塗布法（例えば、スピンコーティング、ディッピング、キャスト法、ＬＢ法、インクジェット法等）により薄膜を形成する。ここで真空蒸着法や溶液塗布法等によって層を形成すると、結晶化等が起こりにくく経時安定性に優れる。また塗布法で成膜する場合は、適当なバインダー樹脂と組み合わせて膜を形成することもできる。 In the organic light-emitting device of the present invention, the layer containing the organic compound according to the present invention and the layer made of other organic compounds are formed by the following method. In general, a thin film is formed by a vacuum deposition method, an ionization deposition method, sputtering, plasma, or a known coating method (for example, spin coating, dipping, casting method, LB method, inkjet method, etc.) after dissolving in an appropriate solvent. Here, when a layer is formed by a vacuum deposition method, a solution coating method, or the like, crystallization or the like hardly occurs and the temporal stability is excellent. Moreover, when forming into a film by the apply | coating method, a film | membrane can also be formed combining with a suitable binder resin.
上記バインダー樹脂としては、ポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ＡＢＳ樹脂、アクリル樹脂、ポリイミド樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらバインダー樹脂は、ホモポリマー又は共重合体として１種単独で使用してもよいし、２種以上を混合して使用してもよい。さらに必要に応じて、公知の可塑剤、酸化防止剤、紫外線吸収剤等の添加剤を併用してもよい。 Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, urea resin, and the like. . Moreover, these binder resins may be used alone as a homopolymer or a copolymer, or may be used as a mixture of two or more. Furthermore, you may use together additives, such as a well-known plasticizer, antioxidant, and an ultraviolet absorber, as needed.
本発明の有機発光素子は、表示装置や照明装置の構成部材として用いることができる。他にも電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライト等の用途がある。 The organic light-emitting element of the present invention can be used as a constituent member of a display device or a lighting device. Other uses include an exposure light source for an electrophotographic image forming apparatus and a backlight for a liquid crystal display.
ここで上述の表示装置は、本発明の有機発光素子を表示部に有する。この表示部は複数の画素を有する。そしてこの画素は本発明の有機発光素子と、発光輝度を制御するためのスイッチング素子の一例であるＴＦＴ素子とを有し、この有機発光素子の陽極又は陰極とＴＦＴ素子のドレイン電極又はソース電極とが電気接続されている。ここで表示装置は、ＰＣ等の画像表示装置として用いることができる。 Here, the display device described above has the organic light-emitting element of the present invention in the display portion. This display unit has a plurality of pixels. The pixel includes the organic light-emitting element of the present invention and a TFT element which is an example of a switching element for controlling light emission luminance. Are electrically connected. Here, the display device can be used as an image display device such as a PC.
表示装置は、エリアＣＣＤ、リニアＣＣＤ、メモリーカード等からの画像情報を入力する入力部を有し、入力された画像を表示部に出力する画像入力装置でもよい。また、撮像装置やインクジェットプリンタが有する表示部として、外部から入力された画像情報を表示する画像出力機能と操作パネルとして画像への加工情報を入力する入力機能との両方を有していてもよい。また表示装置はマルチファンクションプリンタの表示部に用いられてもよい。 The display device may include an input unit that inputs image information from an area CCD, linear CCD, memory card, or the like, and may be an image input device that outputs an input image to the display unit. In addition, the display unit included in the imaging apparatus or the ink jet printer may have both an image output function for displaying image information input from the outside and an input function for inputting processing information to the image as an operation panel. . The display device may be used for a display unit of a multifunction printer.
次に、本発明の有機発光素子を使用した表示装置について図１を用いて説明する。 Next, a display device using the organic light emitting device of the present invention will be described with reference to FIG.
図１は、本発明の有機発光素子と、この有機発光素子に電気接続するスイッチング素子の一例であるＴＦＴ素子と、を有する表示装置の例を示す断面模式図である。図１の表示装置２０は、有機発光素子とＴＦＴ素子との組み合わせが２組図示されている。構造の詳細を以下に説明する。
FIG. 1 is a schematic cross-sectional view showing an example of a display device having the organic light-emitting element of the present invention and a TFT element which is an example of a switching element electrically connected to the organic light-emitting element. The
図１の表示装置２０は、ガラス等の基板１とその上部にＴＦＴ素子又は有機化合物層を保護するための防湿膜２が設けられている。また符号３は金属のゲート電極３である。符号４はゲート絶縁膜４であり、５は半導体層である。
The
ＴＦＴ素子８は半導体層５とドレイン電極６とソース電極７とを有している。ＴＦＴ素子８の上部には絶縁膜９が設けられている。コンタクトホール１０を介して有機発光素子の陽極１１とソース電極７とが接続されている。表示装置はこの構成に限られず、陽極又は陰極のうちいずれか一方とＴＦＴ素子ソース電極又はドレイン電極のいずれか一方とが接続されていればよい。
The TFT element 8 has a semiconductor layer 5, a
尚、図１の表示装置２０において、有機化合物層１２は、単層あるいは多層の有機化合物層を１つの層の如く図示をしている。陰極１３の上には有機発光素子の劣化を抑制するための第一の保護層１４や第二の保護層１５が設けられている。
In the
本発明の表示装置において、スイッチング素子に特に制限はなく、単結晶シリコン基板やＭＩＭ素子、ａ−Ｓｉ型の素子等を用いてもよい。 In the display device of the present invention, the switching element is not particularly limited, and a single crystal silicon substrate, an MIM element, an a-Si type element, or the like may be used.
以下、実施例により本発明を説明する。ただし本発明はこれらに限定されるものではない。尚、後述する実施例のうち、実施例１乃至２２は、本発明に該当する。 Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited to these. Of the examples described later, Examples 1 to 22 correspond to the present invention.
［実施例１］例示化合物ＸＸ−１の合成 [Example 1] Synthesis of Exemplified Compound XX-1
（１）化合物Ｘ３の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ１：４．０ｇ（１３ｍｍｏｌ）
化合物Ｘ２：２．８ｇ（１３ｍｍｏｌ）
エタノール：６５ｍｌ
(1) Synthesis of Compound X3 The following reagents and solvent were charged into the reaction vessel.
Compound X1: 4.0 g (13 mmol)
Compound X2: 2.8 g (13 mmol)
Ethanol: 65ml
次に、反応溶液を６０℃まで加熱した後、６Ｍ水酸化ナトリウム水溶液１０ｍｌを滴下した。滴下終了後、反応溶液を８０℃に加熱して、この温度（８０℃）で２時間攪拌した。次に、反応溶液を冷却した後で生じる沈殿を濾取した。次に、得られた沈殿を、水、エタノールで順次洗浄した後、８０℃で減圧加熱乾燥を行うことにより、濃緑色の固体である化合物Ｘ３を６ｇ（収率：８９％）得た。 Next, after heating the reaction solution to 60 ° C., 10 ml of 6M aqueous sodium hydroxide solution was added dropwise. After completion of the dropwise addition, the reaction solution was heated to 80 ° C. and stirred at this temperature (80 ° C.) for 2 hours. Next, the precipitate formed after the reaction solution was cooled was collected by filtration. Next, the obtained precipitate was washed successively with water and ethanol, and then dried under reduced pressure at 80 ° C. to obtain 6 g (yield: 89%) of Compound X3 as a dark green solid.
（２）化合物Ｘ５の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ３：５．０ｇ（１０ｍｍｏｌ）
化合物Ｘ４：６．１ｇ（２１ｍｍｏｌ）
キシレン：１００ｍｌ
(2) Synthesis of Compound X5 The following reagents and solvent were charged into the reaction vessel.
Compound X3: 5.0 g (10 mmol)
Compound X4: 6.1 g (21 mmol)
Xylene: 100ml
次に、反応溶液を１２０℃まで加熱した後、亜硝酸イソアミル６ｇ（２１ｍｍｏｌ）をゆっくり滴下した。次に、反応溶液を１４０℃に加熱して、この温度（１４０℃）で３時間攪拌した。次に、反応溶液を冷却した後、この反応溶液を減圧濃縮することで茶褐色の液体を得た。これをカラムクロマトグラフィー（展開溶媒；トルエン：ヘプタン＝２：３）にて精製した後、クロロホルム／メタノールで再結晶を行うことにより、黄色結晶の化合物Ｘ５を４．６ｇ（収率：６５％）得た。 Next, after heating the reaction solution to 120 ° C., 6 g (21 mmol) of isoamyl nitrite was slowly added dropwise. Next, the reaction solution was heated to 140 ° C. and stirred at this temperature (140 ° C.) for 3 hours. Next, after cooling the reaction solution, the reaction solution was concentrated under reduced pressure to obtain a brown liquid. This was purified by column chromatography (developing solvent; toluene: heptane = 2: 3) and then recrystallized from chloroform / methanol to obtain 4.6 g of yellow crystal compound X5 (yield: 65%). Obtained.
（３）例示化合物ＸＸ−１の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ５：１．０ｇ（１．５ｍｍｏｌ）
化合物Ｘ６：０．５５ｇ（２．２ｍｍｏｌ）
ＤＭＦ：２０ｍｌ
ビス（ジベンジリデンアセトン）パラジウム（０）：０．８４ｇ（１．５ｍｍｏｌ）
１，８―ジアザビシクロ［５．４．０］ウンデセ−７−エン：０．４４ｇ（２．９ｍｍｏｌ）
トリシクロヘキシルフォスフィン：０．８１ｇ（２．９ｍｍｏｌ）
(3) Synthesis of Exemplified Compound XX-1 The following reagents and solvent were charged into the reaction vessel.
Compound X5: 1.0 g (1.5 mmol)
Compound X6: 0.55 g (2.2 mmol)
DMF: 20ml
Bis (dibenzylideneacetone) palladium (0): 0.84 g (1.5 mmol)
1,8-diazabicyclo [5.4.0] undec-7-ene: 0.44 g (2.9 mmol)
Tricyclohexylphosphine: 0.81 g (2.9 mmol)
次に、反応溶液を１５０℃に加熱して、この温度（１５０℃）で４時間攪拌を行った。次に、反応溶液を冷却した後、この反応溶液を減圧濃縮することで赤黒色固体を得た。次に、得られた固体をカラムクロマトグラフィー（展開溶媒；トルエン：ヘプタン＝１：３）にて精製した後、クロロホルム／メタノールで再結晶することにより、暗赤色の例示化合物ＸＸ−１を２４７ｍｇ（収率：２６％）得た。 Next, the reaction solution was heated to 150 ° C. and stirred at this temperature (150 ° C.) for 4 hours. Next, after cooling the reaction solution, the reaction solution was concentrated under reduced pressure to obtain a red-black solid. Next, the obtained solid was purified by column chromatography (developing solvent; toluene: heptane = 1: 3), and then recrystallized from chloroform / methanol to obtain 247 mg (Example XX-1 of dark red exemplified compound XX-1). (Yield: 26%).
この化合物の純度を、ＨＰＬＣを用いて評価したところ、純度９９％以上であることを確認した。 When the purity of this compound was evaluated using HPLC, it was confirmed that the purity was 99% or more.
また例示化合物ＸＸ−１のトルエン溶液（１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。具体的には、日立製Ｆ−４５００を用いて、３５０ｎｍの励起波長におけるフォトルミネッセンスの測定を行った。その結果、５５０ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (1 * 10 < -5 > mol / L) of exemplary compound XX-1 was measured. Specifically, photoluminescence at an excitation wavelength of 350 nm was measured using Hitachi F-4500. As a result, an emission spectrum having a maximum intensity at 550 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。 Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝５６３．２ DART-TOF-MASS: M + H = 563.2
［実施例２］例示化合物ＸＸ−２の合成 [Example 2] Synthesis of Exemplified Compound XX-2
（１）化合物Ｘ８の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ７：１０ｇ（５５ｍｍｏｌ）
化合物Ｘ２：１２ｇ（５５ｍｍｏｌ）
エタノール：２００ｍｌ
(1) Synthesis of Compound X8 The following reagents and solvent were charged into the reaction vessel.
Compound X7: 10 g (55 mmol)
Compound X2: 12 g (55 mmol)
Ethanol: 200ml
次に、反応溶液を６０℃まで加熱した後、６Ｍ水酸化ナトリウム水溶液２０ｍｌを滴下した。滴下終了後、反応溶液を８０℃に加熱して、この温度（８０℃）で２時間攪拌した。次に、反応溶液を冷却した後で生じる沈殿を濾取した。次に、得られた沈殿を、水、エタノールで順次洗浄した後、８０℃で減圧加熱乾燥を行うことにより、濃緑色の固体である化合物Ｘ８を１８ｇ（収率：９２％）得た。 Next, after heating the reaction solution to 60 ° C., 20 ml of 6M aqueous sodium hydroxide solution was added dropwise. After completion of the dropwise addition, the reaction solution was heated to 80 ° C. and stirred at this temperature (80 ° C.) for 2 hours. Next, the precipitate formed after the reaction solution was cooled was collected by filtration. Next, the obtained precipitate was washed successively with water and ethanol, and then dried under reduced pressure at 80 ° C., thereby obtaining 18 g (yield: 92%) of Compound X8 as a dark green solid.
（２）化合物Ｘ９の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ８：１０ｇ（２８ｍｍｏｌ）
化合物Ｘ４：１７ｇ（５６ｍｍｏｌ）
キシレン：１００ｍｌ
(2) Synthesis of Compound X9 The following reagents and solvent were charged into the reaction vessel.
Compound X8: 10 g (28 mmol)
Compound X4: 17 g (56 mmol)
Xylene: 100ml
次に、反応溶液を１２０℃まで加熱した後、亜硝酸イソアミル６．６ｇ（５６ｍｍｏｌ）をゆっくり滴下した。次に、反応溶液を１４０℃に加熱して、この温度（１４０℃）で３時間攪拌した。次に、反応溶液を冷却した後、この反応溶液を減圧濃縮することで茶褐色の液体を得た。これをカラムクロマトグラフィー（展開溶媒；トルエン：ヘプタン＝２：３）にて精製した後、クロロホルム／メタノールで再結晶を行うことにより、黄色結晶の化合物Ｘ９を９．６ｇ（収率：６１％）得た。 Next, after heating the reaction solution to 120 ° C., 6.6 g (56 mmol) of isoamyl nitrite was slowly added dropwise. Next, the reaction solution was heated to 140 ° C. and stirred at this temperature (140 ° C.) for 3 hours. Next, after cooling the reaction solution, the reaction solution was concentrated under reduced pressure to obtain a brown liquid. This was purified by column chromatography (developing solvent; toluene: heptane = 2: 3) and then recrystallized from chloroform / methanol to obtain 9.6 g of yellow crystal compound X9 (yield: 61%). Obtained.
（３）例示化合物ＸＸ−２の合成
以下に示す試薬、溶媒を反応容器内に投入した。
化合物Ｘ９：２．０ｇ（３．６ｍｍｏｌ）
化合物Ｘ１０：２．０ｇ（５．３ｍｍｏｌ）
ＤＭＦ：４０ｍｌ
ビス（ジベンジリデンアセトン）パラジウム（０）：２．０ｇ（３．６ｍｍｏｌ）
１，８―ジアザビシクロ［５．４．０］ウンデセ−７−エン：１．１ｇ（７．１ｍｍｏｌ）
トリシクロヘキシルフォスフィン：２．０ｇ（７．１ｍｍｏｌ）
(3) Synthesis of Exemplary Compound XX-2 Reagents and solvents shown below were charged into the reaction vessel.
Compound X9: 2.0 g (3.6 mmol)
Compound X10: 2.0 g (5.3 mmol)
DMF: 40ml
Bis (dibenzylideneacetone) palladium (0): 2.0 g (3.6 mmol)
1,8-diazabicyclo [5.4.0] undec-7-ene: 1.1 g (7.1 mmol)
Tricyclohexylphosphine: 2.0 g (7.1 mmol)
次に、反応溶液を１５０℃に加熱して、この温度（１５０℃）で４時間攪拌を行った。次に、反応溶液を冷却した後、この反応溶液を減圧濃縮することで赤黒色固体を得た。次に、得られた固体をカラムクロマトグラフィー（展開溶媒；トルエン：ヘプタン＝１：３）にて精製した後、クロロホルム／メタノールで再結晶することにより、暗赤色の例示化合物ＸＸ−２を５８０ｍｇ（収率：２５％）得た。 Next, the reaction solution was heated to 150 ° C. and stirred at this temperature (150 ° C.) for 4 hours. Next, after cooling the reaction solution, the reaction solution was concentrated under reduced pressure to obtain a red-black solid. Next, the obtained solid was purified by column chromatography (developing solvent; toluene: heptane = 1: 3), and then recrystallized from chloroform / methanol to obtain 580 mg of dark red exemplified compound XX-2 ( (Yield: 25%).
この化合物の純度を、ＨＰＬＣを用いて測定したところ、純度９９％以上であることを確認した。 When the purity of this compound was measured using HPLC, it was confirmed that the purity was 99% or more.
また実施例１と同様の方法により、例示化合物ＸＸ−２のトルエン溶液（濃度：１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。その結果、５５０ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (concentration: 1 × 10 −5 mol / L) of exemplary compound XX-2 was measured by the same method as in Example 1. As a result, an emission spectrum having a maximum intensity at 550 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝５６３．２
Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
DART-TOF-MASS: M + H = 563.2
［実施例３］例示化合物ＸＸ−５の合成
実施例２（１）において、化合物Ｘ２に代えて下記に示される化合物Ｘ１１を使用する以外は、実施例２と同様の方法で合成を行うことにより、例示化合物ＸＸ−５を得た。
[Example 3] Synthesis of Exemplified Compound XX-5 In Example 2 (1), except that Compound X11 shown below was used instead of Compound X2, the synthesis was performed in the same manner as in Example 2. Example compound XX-5 was obtained.
この化合物の純度を、ＨＰＬＣを用いて測定したところ、純度９９．５％以上であることを確認した。 When the purity of this compound was measured using HPLC, it was confirmed that the purity was 99.5% or more.
また実施例１と同様の方法により、例示化合物ＸＸ−５のトルエン溶液（濃度：１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。尚、本実施例においては、励起波長を５００ｎｍとした。その結果、５５０ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (concentration: 1 × 10 −5 mol / L) of exemplary compound XX-5 was measured by the same method as in Example 1. In this example, the excitation wavelength was 500 nm. As a result, an emission spectrum having a maximum intensity at 550 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝８０５．３
Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
DART-TOF-MASS: M + H = 805.3
［実施例４］例示化合物ＸＸ−１０の合成
実施例２（１）において、化合物Ｘ７に代えて下記に示される化合物Ｘ１２を使用する以外は、実施例２と同様の方法で合成を行うことにより、例示化合物ＸＸ−１０を得た。
[Example 4] Synthesis of Exemplified Compound XX-10 By synthesizing in the same manner as in Example 2 except that Compound X12 shown below is used instead of Compound X7 in Example 2 (1). Example compound XX-10 was obtained.
この化合物の純度を、ＨＰＬＣを用いて測定したところ、純度９９．５％以上であることを確認した。 When the purity of this compound was measured using HPLC, it was confirmed that the purity was 99.5% or more.
また実施例１と同様の方法により、例示化合物ＸＸ−１０のトルエン溶液（濃度：１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。尚、本実施例においては、励起波長を５００ｎｍとした。その結果、５５０ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (concentration: 1 × 10 −5 mol / L) of Exemplified Compound XX-10 was measured by the same method as in Example 1. In this example, the excitation wavelength was 500 nm. As a result, an emission spectrum having a maximum intensity at 550 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝８０５．３
Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
DART-TOF-MASS: M + H = 805.3
［実施例５］例示化合物ＸＹ−１の合成
実施例１（３）において、化合物Ｘ６の代わりに下記に示されるＸ１３を使用する以外は、実施例１と同様の方法で合成を行うことにより、例示化合物ＸＹ−１を得た。
Example 5 Synthesis of Exemplified Compound XY-1 In Example 1 (3), synthesis was carried out in the same manner as in Example 1 except that X13 shown below was used instead of compound X6. Exemplary compound XY-1 was obtained.
この化合物の純度を、ＨＰＬＣを用いて測定したところ、純度９９．５％以上であることを確認した。 When the purity of this compound was measured using HPLC, it was confirmed that the purity was 99.5% or more.
また実施例１と同様の方法により、例示化合物ＸＹ−１のトルエン溶液（濃度：１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。尚、本実施例においては、励起波長を４５０ｎｍとした。その結果、５５３ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (concentration: 1 × 10 −5 mol / L) of the exemplary compound XY-1 was measured by the same method as in Example 1. In this example, the excitation wavelength was 450 nm. As a result, an emission spectrum having a maximum intensity at 553 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝７６５．３
Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
DART-TOF-MASS: M + H = 765.3
［実施例６］例示化合物ＸＹ−３の合成
実施例２（１）において、化合物Ｘ２の代わりに下記に示されるＸ１４を使用する以外は、実施例２と同様の方法で合成を行うことにより、例示化合物ＸＹ−３を得た。
Example 6 Synthesis of Exemplified Compound XY-3 In Example 2 (1), synthesis was carried out in the same manner as in Example 2 except that X14 shown below was used instead of compound X2. Exemplary compound XY-3 was obtained.
この化合物の純度を、ＨＰＬＣを用いて測定したところ、純度９９．５％以上であることを確認した。 When the purity of this compound was measured using HPLC, it was confirmed that the purity was 99.5% or more.
また実施例１と同様の方法により、例示化合物ＸＹ−１のトルエン溶液（濃度：１×１０-5ｍｏｌ／Ｌ）における発光スペクトルを測定した。尚、本実施例においては、励起波長を４５０ｎｍとした。その結果、５５２ｎｍに最大強度を有する発光スペクトルを得た。 Moreover, the emission spectrum in the toluene solution (concentration: 1 × 10 −5 mol / L) of the exemplary compound XY-1 was measured by the same method as in Example 1. In this example, the excitation wavelength was 450 nm. As a result, an emission spectrum having a maximum intensity at 552 nm was obtained.
また日本電子（ＪＥＯＬ）社製、ＪＭＳ−Ｔ１００ＴＤ（ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ）を用いて分子量を測定することで同定した。
ＤＡＲＴ−ＴＯＦ−ＭＡＳＳ：Ｍ＋Ｈ＝８７７．５
Moreover, it identified by measuring the molecular weight using JEOL (JEOL) company make and JMS-T100TD (DART-TOF-MASS).
DART-TOF-MASS: M + H = 877.5
［実施例７］
本実施例では、基板上に、陽極、ホール注入層、ホール輸送層、発光層、ホール・エキシトンブロッキング層、電子輸送層、陰極が順次形成された有機発光素子を作製した。以下に、本実施例で使用した材料の一部を示す。
[Example 7]
In this example, an organic light emitting device in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, a hole / exciton blocking layer, an electron transport layer, and a cathode were sequentially formed on a substrate was produced. Below, some of the materials used in this example are shown.
まずガラス基板上に、ＩＴＯを成膜し、所望のパターニング加工を施すことによりＩＴＯ電極（陽極）を形成した。このときＩＴＯ電極の膜厚を１００ｎｍとした。このようにＩＴＯ電極が形成された基板をＩＴＯ基板として、以下の工程で使用した。 First, an ITO film was formed on a glass substrate, and an ITO electrode (anode) was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps.
次に、１×１０-5Ｐａの真空チャンバー内における抵抗加熱による真空蒸着を行って、上記ＩＴＯ基板上に、下記表４に示す有機化合物層及び電極層を連続成膜した。尚、このとき対向する電極（金属電極層、陰極）の電極面積が３ｍｍ2となるようにした。 Next, vacuum deposition was performed by resistance heating in a vacuum chamber of 1 × 10 −5 Pa, and an organic compound layer and an electrode layer shown in Table 4 below were continuously formed on the ITO substrate. At this time, the electrode area of the opposing electrodes (metal electrode layer, cathode) was set to 3 mm 2 .
尚、本実施例において、Ｇ−２及びＧ−３は、いずれも表３に示されるＨ１である。即ち、本実施例の有機発光素子において、発光層は、表３中のＨ１をホストとし、例示化合物ＸＸ−１をゲストとする２成分系の層とも解釈することができる。 In this example, G-2 and G-3 are all H1 shown in Table 3. That is, in the organic light-emitting device of this example, the light-emitting layer can be interpreted as a two-component layer in which H1 in Table 3 is a host and Exemplified Compound XX-1 is a guest.
得られた素子について、素子の特性を測定・評価した。具体的には、電流電圧特性をヒューレッドパッカード社製・微小電流計４１４０Ｂで測定し、発光輝度は、トプコン社製ＢＭ７で測定した。測定の結果を表５に示す。 About the obtained element, the characteristic of the element was measured and evaluated. Specifically, the current-voltage characteristic was measured with a micro ammeter 4140B manufactured by Hured Packard, and the light emission luminance was measured with a BM7 manufactured by Topcon. Table 5 shows the measurement results.
［実施例８乃至１７］
実施例７において、Ｇ−２、Ｇ−３及びゲストを、表５に示される化合物に適宜変更する以外は、実施例７と同様の方法により有機発光素子を作製した。得られた素子について実施例７と同様に素子の特性を測定・評価した。測定の結果を表５に示す。尚、表５において、Ｇ−２として使用したＨ２、Ｈ７、Ｈ１０、Ｈ１５、Ｈ１７、Ｈ１９、Ｈ２１及びＨ２３、並びにＧ−３として使用したＨ２、Ｈ７、Ｈ１０、Ｈ１７、Ｈ１９、Ｈ２１、Ｈ２３及びＨ２４は、それぞれ表３に示されるホストである。
[Examples 8 to 17]
In Example 7, an organic light-emitting device was produced in the same manner as in Example 7 except that G-2, G-3, and the guest were appropriately changed to the compounds shown in Table 5. About the obtained element, the characteristic of the element was measured and evaluated in the same manner as in Example 7. Table 5 shows the measurement results. In Table 5, H2, H7, H10, H15, H17, H19, H21 and H23 used as G-2, and H2, H7, H10, H17, H19, H21, H23 and H24 used as G-3. Are the hosts shown in Table 3, respectively.
［実施例１８］
本実施例では、基板上に、陽極、ホール注入層、ホール輸送層、発光層、電子輸送層、電子注入層、陰極が順次形成された有機発光素子を作製した。尚、本実施例で作製される有機発光素子は共振構造を有している。以下に、本実施例で使用した材料の一部を示す。
[Example 18]
In this example, an organic light emitting device was fabricated in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate. In addition, the organic light emitting device manufactured in this example has a resonance structure. Below, some of the materials used in this example are shown.
まずスパッタリング法により、ガラス基板（支持体）上に、アルミニウム合金（ＡｌＮｄ）を成膜し反射性陽極を形成した。このとき反射性陽極の膜厚を１００ｎｍとした。次に、スパッタリング法により、反射性陽極上にＩＴＯを成膜し透明性陽極を形成した。このとき透明性陽極の膜厚を８０ｎｍとした。次に、この陽極の周辺にアクリル製の素子分離膜を膜厚１．５μｍで形成した後、所望のパターニング成形を行い、半径３ｍｍの開口部を設けた。次に、陽極が形成されている基板を、アセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄した。次に、ＩＰＡで煮沸洗浄してから乾燥させた。次に、この基板表面に対してＵＶ／オゾン洗浄を施した。 First, an aluminum alloy (AlNd) was formed on a glass substrate (support) by a sputtering method to form a reflective anode. At this time, the thickness of the reflective anode was set to 100 nm. Next, ITO was formed into a film on the reflective anode by a sputtering method to form a transparent anode. At this time, the film thickness of the transparent anode was 80 nm. Next, after forming an acrylic element isolation film with a film thickness of 1.5 μm around the anode, desired patterning was performed to provide an opening with a radius of 3 mm. Next, the substrate on which the anode was formed was sequentially ultrasonically washed with acetone and isopropyl alcohol (IPA). Next, it was dried by boiling with IPA and then dried. Next, this substrate surface was subjected to UV / ozone cleaning.
次に、１×１０-5Ｐａの真空チャンバー内における抵抗加熱による真空蒸着を行って、上記ＩＴＯ基板上に、下記表６に示す有機化合物層を連続成膜した。 Next, vacuum deposition was performed by resistance heating in a vacuum chamber of 1 × 10 −5 Pa, and organic compound layers shown in Table 6 below were continuously formed on the ITO substrate.
尚、本実施例において、Ｇ−１３及びＧ−１４は、いずれも表３に示されるＨ１０である。即ち、本実施例の有機発光素子において、発光層は、表３中のＨ１０をホストとし、例示化合物ＸＸ−１をゲストとする２成分系の層とも解釈することができる。 In this example, G-13 and G-14 are both H10 shown in Table 3. That is, in the organic light-emitting device of this example, the light-emitting layer can be interpreted as a two-component layer in which H10 in Table 3 is the host and exemplary compound XX-1 is the guest.
次に、スパッタリング法により、電子注入層上に、ＩＺＯを成膜して陰極を形成した。このとき陰極の膜厚を３０ｎｍとした。最後に、窒素雰囲気下において封止を行った。
以上により、有機発光素子を作製した。
Next, a cathode was formed by depositing IZO on the electron injection layer by sputtering. At this time, the thickness of the cathode was set to 30 nm. Finally, sealing was performed in a nitrogen atmosphere.
Thus, an organic light emitting device was produced.
得られた素子について、素子の特性を測定・評価した。具体的には、電流電圧特性をヒューレッドパッカード社製・微小電流計４１４０Ｂで測定し、発光輝度は、トプコン社製ＢＭ７で測定した。測定の結果を表７に示す。 About the obtained element, the characteristic of the element was measured and evaluated. Specifically, the current-voltage characteristic was measured with a micro ammeter 4140B manufactured by Hured Packard, and the light emission luminance was measured with a BM7 manufactured by Topcon. Table 7 shows the measurement results.
［実施例１９乃至２０］
実施例１８において、Ｇ−１３、Ｇ−１４及びゲストを、表７に示される化合物に適宜変更する以外は、実施例１８と同様の方法により有機発光素子を作製した。得られた素子について実施例１８と同様に素子の特性を測定・評価した。測定の結果を表７に示す。尚、表７において、Ｇ−１３として使用したＨ６及びＨ１６、並びにＧ−１４として使用したＨ２１及びＨ２４は、それぞれ表３に示されるホストである。
[Examples 19 to 20]
In Example 18, an organic light-emitting device was produced in the same manner as in Example 18 except that G-13, G-14, and the guest were appropriately changed to the compounds shown in Table 7. The device characteristics of the obtained device were measured and evaluated in the same manner as in Example 18. Table 7 shows the measurement results. In Table 7, H6 and H16 used as G-13, and H21 and H24 used as G-14 are hosts shown in Table 3, respectively.
［実施例２１］
本実施例では、基板上に、陽極、ホール輸送層、第１発光層、第２発光層、ホール・エキシトンブロッキング層、電子輸送層、陰極が順次形成された有機発光素子を作製した。尚、本実施例の有機発光素子は発光層が複数あるので、各発光層に含まれるゲストが個別あるいは同時に発光する態様である。以下に、本実施例で使用した材料の一部を示す。
[Example 21]
In this example, an organic light emitting device was fabricated in which an anode, a hole transport layer, a first light emitting layer, a second light emitting layer, a hole / exciton blocking layer, an electron transport layer, and a cathode were sequentially formed on a substrate. In addition, since the organic light emitting element of a present Example has multiple light emitting layers, it is the aspect which the guest contained in each light emitting layer light-emits separately or simultaneously. Below, some of the materials used in this example are shown.
まずガラス基板上に、ＩＴＯを成膜し、所望のパターニング加工を施すことによりＩＴＯ電極を形成した。このときＩＴＯ電極の膜厚を１００ｎｍとした。このようにＩＴＯ電極が形成された基板をＩＴＯ基板として、以下の工程で使用した。 First, ITO was formed on a glass substrate, and an ITO electrode was formed by performing a desired patterning process. At this time, the film thickness of the ITO electrode was 100 nm. The substrate on which the ITO electrode was thus formed was used as an ITO substrate in the following steps.
次に、１×１０-5Ｐａの真空チャンバー内における抵抗加熱による真空蒸着を行って、上記ＩＴＯ基板上に、下記表８に示す有機化合物層及び電極層を連続成膜した。尚、このとき対向する電極（金属電極層、陰極）の電極面積が３ｍｍ2となるようにした。 Next, vacuum deposition was performed by resistance heating in a vacuum chamber of 1 × 10 −5 Pa, and an organic compound layer and an electrode layer shown in Table 8 below were continuously formed on the ITO substrate. At this time, the electrode area of the opposing electrodes (metal electrode layer, cathode) was set to 3 mm 2 .
尚、本実施例において、Ｇ−２２、Ｇ−２３及びＧ−２４は、それぞれ表３に示されるＨ１０、Ｈ２３、Ｈ８である。 In this embodiment, G-22, G-23, and G-24 are H10, H23, and H8 shown in Table 3, respectively.
得られた素子について、素子の特性を測定・評価した。具体的には、電流電圧特性をヒューレッドパッカード社製・微小電流計４１４０Ｂで測定し、発光輝度は、トプコン社製ＢＭ７で測定した。測定の結果を表９に示す。 About the obtained element, the characteristic of the element was measured and evaluated. Specifically, the current-voltage characteristic was measured with a micro ammeter 4140B manufactured by Hured Packard, and the light emission luminance was measured with a BM7 manufactured by Topcon. Table 9 shows the measurement results.
［実施例２２、２３］
実施例２１において、Ｇ−２２、Ｇ−２３、Ｇ−２４及びゲストを、表９に示される化合物に適宜変更する以外は、実施例２２と同様の方法により有機発光素子を作製した。得られた素子について実施例２２と同様に素子の特性を測定・評価した。測定の結果を表９に示す。尚、表９において、Ｇ−２２として使用したＨ１８及びＨ２３、Ｇ−２３として使用したＨ１８及びＨ２３、並びにＧ−２４として使用したＨ４及びＨ１０は、それぞれ表３に示されるホストである。
[Examples 22 and 23]
In Example 21, an organic light emitting device was produced in the same manner as in Example 22 except that G-22, G-23, G-24 and the guest were appropriately changed to the compounds shown in Table 9. About the obtained element, the characteristic of the element was measured and evaluated in the same manner as in Example 22. Table 9 shows the measurement results. In Table 9, H18 and H23 used as G-22, H18 and H23 used as G-23, and H4 and H10 used as G-24 are hosts shown in Table 3, respectively.
以上説明したように、本発明に係る有機化合物は、高い量子収率と黄色に適した発光を有する化合物である。このため本発明に係る有機化合物を有機発光素子の構成材料として用いた場合、良好な発光特性を有する発光素子を得ることができる。 As described above, the organic compound according to the present invention is a compound having a high quantum yield and light emission suitable for yellow. For this reason, when the organic compound according to the present invention is used as a constituent material of an organic light-emitting device, a light-emitting device having good light-emitting characteristics can be obtained.
８：ＴＦＴ素子、１１：陽極、１２：有機化合物層、１３：陰極 8: TFT element, 11: anode, 12: organic compound layer, 13: cathode
Claims (12)
前記Ｒ 3 乃至Ｒ 8 及び前記Ｒ 11 乃至Ｒ 20 のいずれかが、炭素数１乃至４のアルキル基を有してもよいアリール基であることを特徴とする、請求項１に記載の有機化合物。 Any one of R 1 and R 10 or R 2 and R 9 is an aryl group, pyrimidyl group and pyrazyl group which may have an alkyl group having 1 to 4 carbon atoms, and the other is A hydrogen atom,
2. The organic compound according to claim 1, wherein any one of R 3 to R 8 and R 11 to R 20 is an aryl group which may have an alkyl group having 1 to 4 carbon atoms . .
３のいずれか一項に記載の有機化合物。 The organic compound according to any one of claims 1 to 3, which has two or more tertiary butyl groups in the molecular structure.
前記陽極と前記陰極との間に配置される有機化合物層と、を有する有機発光素子であって、
前記有機化合物層の少なくとも一層に、請求項１乃至４のいずれか一項に記載の有機化合物が含まれることを特徴とする、有機発光素子。 An anode and a cathode;
An organic light emitting device having an organic compound layer disposed between the anode and the cathode,
An organic light-emitting element, wherein the organic compound according to claim 1 is contained in at least one layer of the organic compound layer.
子。 The organic light emitting device according to claim 5, wherein the organic compound is contained in a light emitting layer.
前記複数の画素が、請求項５乃至７のいずれか一項に記載の有機発光素子と、前記有機発光素子に電気接続されるＴＦＴ素子と、をそれぞれ有することを特徴とする、表示装置。 A display device having a plurality of pixels,
The display device, wherein each of the plurality of pixels includes the organic light emitting element according to claim 5 and a TFT element electrically connected to the organic light emitting element.
前記表示部が複数の画素を有し、
前記複数の画素が、請求項５乃至７のいずれか一項に記載の有機発光素子と、前記有機発光素子に電気接続されるＴＦＴ素子と、をそれぞれ有することを特徴とする、画像入力装置。 An image input device having an input unit for inputting image information and a display unit for outputting an image,
The display unit includes a plurality of pixels;
The image input device, wherein each of the plurality of pixels includes the organic light emitting element according to claim 5 and a TFT element electrically connected to the organic light emitting element.
装置。 An illuminating device comprising the organic light-emitting element according to claim 5.
前記露光光源が、請求項５乃至７のいずれか一項に記載の有機発光素子を有することを特徴とする、画像形成装置。 An electrophotographic image forming apparatus having an exposure light source,
An image forming apparatus, wherein the exposure light source includes the organic light-emitting element according to claim 5.
前記露光光源は、請求項５乃至７のいずれか一項に記載の有機発光素子を有することを特徴とする、露光光源。The said exposure light source has an organic light emitting element as described in any one of Claims 5 thru | or 7, The exposure light source characterized by the above-mentioned.
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